Biobased Epoxy Resins from Deconstructed Native Softwood Lignin

Pas, Daniel J. van de; Torr, Kirk M.

doi:10.1021/acs.biomac.7b00767

Cited by 112 publications

(112 citation statements)

References 54 publications

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“…Van de Pas and Torr 394 used the oil from mild hydrogenolysis of pinewood to react with epichlorohydrin to give epoxy prepolymers ( Figure 34 ). After fractionation in diethyl ether, they obtained two fractions named hydrogenolysis epoxy prepolymers (LHEP) and oligomeric lignin hydrogenolysis epoxy prepolymers (LHOEP).…”

Section: Lignin-derived Monomers To Biobased Polymers or Polymer Builmentioning

confidence: 99%

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Bright Side of Lignin Depolymerization: Toward New Platform Chemicals

et al. 2018

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Lignin, a major component of lignocellulose, is the largest source of aromatic building blocks on the planet and harbors great potential to serve as starting material for the production of biobased products. Despite the initial challenges associated with the robust and irregular structure of lignin, the valorization of this intriguing aromatic biopolymer has come a long way: recently, many creative strategies emerged that deliver defined products via catalytic or biocatalytic depolymerization in good yields. The purpose of this review is to provide insight into these novel approaches and the potential application of such emerging new structures for the synthesis of biobased polymers or pharmacologically active molecules. Existing strategies for functionalization or defunctionalization of lignin-based compounds are also summarized. Following the whole value chain from raw lignocellulose through depolymerization to application whenever possible, specific lignin-based compounds emerge that could be in the future considered as potential lignin-derived platform chemicals.

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Section: Lignin-derived Monomers To Biobased Polymers or Polymer Builmentioning

confidence: 99%

Section: Lignin-derived Monomers To Biobased Polymers or Polymer Builmentioning

confidence: 99%

Bright Side of Lignin Depolymerization: Toward New Platform Chemicals

et al. 2018

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“…Thus, in the view of decreasing the environmental impact, saving petroleum resources and replacing toxic BPA for the synthesis of epoxy, bio-based thermosets are widely studied. During the last decades many research works have therefore been dedicated to the specific domain of bio-based epoxy thermosets pointing out the potential of rosin, 4 cardanol, 5 iso-eugenol, 6,7 eugenol, [8][9][10][11][12] , vegetable oil, 13 modified lignin, [14][15][16] vanillin, [17][18][19] terpene derivatives, 20 daidzein, 21 ... to replace DGEBA epoxy monomer. Among the most promising feedstocks to replace BPA, building blocks derived from lignin, have been particularly pointed out.…”

Section: Introductionmentioning

confidence: 99%

New Reactive Isoeugenol Based Phosphate Flame Retardant: Toward Green Epoxy Resins

Pourchet

Sonnier

Ben-Abdelkader

et al. 2019

ACS Sustainable Chem. Eng.

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A bio-based reactive phosphate flame retardant derived from iso-eugenol was synthesized and fully characterized (1 H, 13 C, 31 P NMR, FTIR, MS) with the aim of improving flame retardancy behavior of bio-based epoxy thermosets. This new green flame retardant, diepoxy-iso-eugenol phenylphosphate (DEpiEPP) was then copolymerized either with conventional diglycidylether of bisphenol A resin (DGEBA) or with a totally bio-based glycidylether epoxy iso-eugenol (GEEpiE) resin using a bio-based camphoric anhydride (CA) as hardener. Resulting thermosets with varying rates of flame retardant (1.0 to 4.3 w% phosphorus) were then characterized (FTIR, DSC, nanoindentation, 3-point bending test, TGA, PCFC, cone calorimeter). By this way, a new solution was proposed allowing (i) to increase the bio-based content of thermosets (ii) to improve the flame retardancy properties by a reactive way and (iii) to provide epoxy thermosets with high Tg, excellent mechanical properties and a curing temperature compatible with the use of vegetable fibers. For instance, with a weight content of 2.0 w% P, both GEEpiE-CA-DEpiEPP (95% bio-based content) and partially bio-based DGEBA-CA-DEpiEPP (57% bio-based content) epoxy thermosets possess high Tg (respectively 129 and 105°C), bending elastic modulus and strength of respectively 4.08 GPa and 90 MPa and demonstrate good flameretardant properties due to char promotion showing high promise for application.

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“…This way induces a variability of the resulting materials properties since the content of lignin in different types of biomass resources varies strongly. An alternative approach consists of lignin fragmentation [10][11][12] leading to a wide range of building blocks, such as vanillin [13][14][15], rosin [16], eugenol [17][18][19][20] and isoeugenol [21,22], which are then epoxidized.Within this context, our research team has recently described both the synthesis of an epoxy monomer derived from isoeugenol, named as GlycidylEther Epoxy isoeugenol (GEEpiE) [21], and its curing with camphoric anhydride [22]. Behaviours of the resulting thermoset are consistent with its use as a bio-based epoxy matrix for structural composites.…”

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confidence: 99%

New Eco-Friendly Synthesized Thermosets from Isoeugenol-Based Epoxy Resins

et al. 2020

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Epoxy resin plays a key role in composite matrices and DGEBA is the major precursor used. With the aim of favouring the use of bio resources, epoxy resins can be prepared from lignin. In particular, diglycidyl ether of isoeugenol derivatives are good candidates for the replacement of DGEBA. This article presents an effective and eco-friendly way to prepare epoxy resin derived from isoeugenol (BioIgenox), making its upscale possible. BioIgenox has been totally characterized by NMR, FTIR, MS and elemental analyses. Curing of BioIgenox and camphoric anhydride with varying epoxide function/anhydride molar ratios has allowed determining an optimum ratio near 1/0.9 based on DMA and DSC analyses and swelling behaviours. This thermoset exhibits a Tg measured by DMA of 165 °C, a tensile storage modulus at 40 °C of 2.2 GPa and mean 3-point bending stiffness, strength and strain at failure of 3.2 GPa, 120 MPa and 6.6%, respectively. Transposed to BioIgenox/hexahydrophtalic anhydride, this optimized formulation gives a thermoset with a Tg determined by DMA of 140 °C and a storage modulus at 40 °C of 2.6 GPa. The thermal and mechanical properties of these two thermosets are consistent with their use as matrices for structural or semi-structural composites.

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Biobased Epoxy Resins from Deconstructed Native Softwood Lignin

Cited by 112 publications

References 54 publications

Bright Side of Lignin Depolymerization: Toward New Platform Chemicals

Bright Side of Lignin Depolymerization: Toward New Platform Chemicals

New Reactive Isoeugenol Based Phosphate Flame Retardant: Toward Green Epoxy Resins

New Eco-Friendly Synthesized Thermosets from Isoeugenol-Based Epoxy Resins

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